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SML1269

Sigma-Aldrich

Cepharanthine

≥95% (HPLC)

Sinônimo(s):

(+)-Cepharanthine, 6′,12′-Dimethoxy-2,2′-dimethyl-6,7-(methylenebis(oxy))oxyacanthan, O-Methylcepharanoline, CEP, Cepharanthin, Cepharantin, NSC 623442, [14aS-(14aR*,26aS*)]-2,3,13,14,14a,15,26,26a-octahydro-22,30-dimethoxy-1,14-dimethyl- H-4,6:16,19-Dietheno-21,25-metheno-12H-[1,3]dioxolo[4,5-g]pyrido[2′,3′:17,18][1,10]dioxacycloeicosino[2,3,4-ij]isoquinoline

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About This Item

Fórmula empírica (Notação de Hill):
C37H38N2O6
Número CAS:
481-49-2
Peso molecular:
606.71
Número MDL:
MFCD00210482
Código UNSPSC:
12352200
ID de substância PubChem:
329825757
NACRES:
NA.77

fonte biológica

(isolated from the tuber of Stephania Cepharantha Hayata (plant).)

Nível de qualidade

100

Ensaio

≥95% (HPLC)

forma

powder

cor

white to beige

solubilidade

DMSO: 10 mg/mL, clear

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

CN1CCC2=CC3=C(OCO3)C(O4)=C2[C@@H]1CC5=CC=C(OC6=C(OC)C=CC(C[C@@H]7C8=CC4=C(OC)C=C8CCN7C)=C6)C=C5

InChI

1S/C37H38N2O6/c1-38-13-11-24-18-31(41-4)33-20-27(24)28(38)16-23-7-10-30(40-3)32(17-23)44-26-8-5-22(6-9-26)15-29-35-25(12-14-39(29)2)19-34-36(37(35)45-33)43-21-42-34/h5-10,17-20,28-29H,11-16,21H2,1-4H3/t28-,29+/m1/s1

chave InChI

YVPXVXANRNDGTA-WDYNHAJCSA-N

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Ações bioquímicas/fisiológicas

Cepharanthine is an anti-inflammatory, antiallergic, immunomo- modulatory and antineoplastic alkaloid isolated from Stephania cepharantha Hayata. Cepharanthine is an inhibitor of efflux transporter ABCC10. Also, Cepharanthine binds to central portion of Hsp90 with Kd 15 nM. Recent studies suggest that Cepharanthine inhibits the entry of HIV-1 by reducing plasma membrane fluidity.
Cepharanthine is known to be the only biscoclaurine alkaloid containing a methylenedioxy group. It promotes leukocytosis, as a result, it might activate the reticular endothelial system, hematopoietic tissue and bone marrow hyperplasia. It is known to inhibit Ehrlich tumor proliferation. Cepharanthine can increase the sensitivity and efficacy of antitumor drugs.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302

Declarações de precaução

P301 + P312 + P330

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Natural Small Molecule Drugs from Plants, 499-499 (2018)
The Alkaloids, 223-223 (2014)
Kouki Matsuda et al.
Bioorganic & medicinal chemistry letters, 24(9), 2115-2117 (2014-04-08)
The anti-HIV-1 activity of cepharanthine (CEP), a natural product derived from Stephania cepharantha Hayata, was evaluated. CEP stabilized plasma membrane fluidity and inhibited HIV-1 envelope-dependent cell-to-cell fusion of HIV-1-infected cells as well as cell-free infection. It is suggested that CEP
Rishil J Kathawala et al.
Chinese journal of cancer, 33(5), 223-230 (2013-10-10)
ABCC10, also known as multidrug-resistant protein 7 (MRP7), is the tenth member of the C subfamily of the ATP-binding cassette (ABC) superfamily. ABCC10 mediates multidrug resistance (MDR) in cancer cells by preventing the intracellular accumulation of certain antitumor drugs. The
Jun Haginaka et al.
Analytical biochemistry, 434(1), 202-206 (2012-12-12)
Heat shock protein 90α (Hsp90α) immobilized on aminopropyl silica gels was prepared via the N- or C-terminal, which was termed Hsp90α-NT or Hsp90α-CT, respectively. Binding interactions of biscoclaurine alkaloids (cepharanthine (CEP), berbamine (BBM), isotetrandrine (ITD), and cycleanine (CCN)) with Hsp90α

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